I’m
a 24-year-old straight female. I just moved to a new city
where I don’t know anyone. So the other night I hung out with
a 21-year-old jock from work. We went to a bar and eventually
wound up back at his apartment where we both smoked pot. I
was thinking he was a muscle-bound meathead so to shock him
I told him a story about one of my male friends wearing a
skirt. He kind of exploded and said, “You have guy friends
who wear skirts? That’s weird because I like to dress up like
a woman and it turns me on and I really want to be a girl
and I want to be pretty and I have these huge muscles because
I’m fighting it and I’ve never told anybody this before and
I can’t believe I just told you and it’s probably because
I’m drunk and do you think it would be okay if someday I dressed
up for you?”

I swear it was like that, one big run-on sentence. We talked
for four hours and he says that he’s not gay. He just wants
to be a woman. The strain of living as two people is really
getting to him, he said, hence the heavy drinking/pot smoking.
I suggested therapy, not to “fix” him but to get to a place
where it doesn’t make him so unhappy. Now I’m not sure what
to do. I can tell that he’s crushing on me. He was before
he told me his big secret, and now that he’s confided his
secret in me, his crush has intensified. I
wasn’t really interested in him to begin with but I must admit
his admission makes him more appealing. I really do want him
to dress up for me, I’m just not sure that I’m ready to deal
with his reaction when I don’t want to live happily ever after—especially
if he sticks with the idea of becoming a woman. I’m just not
sexually interested in actual women.

Would I be helping him come to terms with his identity by
taking part in his masturbatory fantasy? Or would I be scarring
him for life since I’m not interested in anything long-term?
I’m afraid that if I reject him now he’s going to think it’s
because of the cross-dressing.

—Told
Very Titillating Secret

There
are two things you want here, TVTS. You want to see the muscle-bound
21-year-old dressed up in women’s clothes for kicks, and you
want to see the muscle-bound 21-year-old in therapy for his
own good. So why not make dressing up for you contingent upon
him finding a therapist?

Tell him you’re tempted but you’re not going to go there if
you’re the only person he can talk to about this stuff. If
he wants to mess around and explore with you, fine, great,
you’re game for that. But that’s all you’re signing up for.
You can’t be his therapist and you’re not making any commitments.
Explain to him that if you knew you were the only person he
had to talk to about his desires, you would feel obligated
to continue seeing him even if you decided, for any number
of other reasons, that the relationship wasn’t working out.

I guarantee you, TVTS, that he’ll have his first therapy session
scheduled a half-hour after you get off the phone.

This past weekend I went out to a gay bar in Las Vegas.
I consider myself a “hot” 26-year-old guy, but with a lacking
sex life as I am somewhat shy and closeted. Well, several
hours and drinks go by with not so much as a glance from another
boy when who should walk in but sex on wheels himself. He
was a dancer in a Cirque du Soleil production, 22, with looks
and a body that could kill. We talked for a while and played
some pool and decided to go back to my place. When we got
home I ripped off his clothes and we began to play. Hours
later, he was starting to fuck me with a condom on. Then about
five minutes into the fucking, I realized the condom had slipped
off accidentally and he was barebacking me. I immediately
got up and asked him if he was clean and he said yes, even
though I was too freaked out to continue.

Am I just a paranoid freak for worrying about my chances of
getting some type of deadly disease from this encounter? I
don’t think he came in me at all, plus later he said he was
bisexual and very clean. He was only barebacking me for like
a minute or less. Please help, my sanity depends on it.

—Screwed
A Circus Kid

P.S.
Yes, he did do some circus tricks for me . . .

If your sanity depends on hearing me say something like, “There’s
no way you could’ve been infected by that circus kid . . .
” then my response is going to drive you out of your mind.
There are plenty of hot, 22-year-old HIV-positive guys out
there, just as there are plenty of hot guys who got infected
with HIV under the circumstances you describe. Sorry, SACK,
but there’s HIV in pre-come, anal sex is the most efficient
way to spread HIV, and not all guys who claim to be clean
are telling the truth.

So what do you do? You go see a doctor, get tested for HIV
and everything else, and ask if it’s not too late to take
an emergency course of HIV medications. The Centers for Disease
Control and Prevention recently advised doctors to start making
a month-long course of anti-retroviral drugs available to
people who are accidentally exposed to HIV. (It used to be
made available only to medical personnel who were exposed
to HIV on the job.) Josh Bamberger of the San Francisco Department
of Public Health said this to the Associated Press about the
CDC’s new recommendations: “If you had unsafe sex while you
were drunk or had a condom break, you should take these medicines.”
Sounds like you, SACK.

Finally, while plenty of guys have been exposed to HIV under
the circumstances you describe, there are plenty of guys out
there who have had a condom break on them and didn’t wind
up with HIV. To save yourself from this kind of anxiety in
the future, you should reserve anal sex for guys you know
and trust. There are plenty of other things you can do with
a 22-year-old Cirque du Soleil performer, SACK.

You mention quite often in your column the importance
of couples being open to one another’s sexual interests. Usually
these interests are way out there. My issues are completely
mundane. I would like more foreplay, in the form of my boyfriend
paying more attention to my boobs. Thirty minutes of tongue
kissing only makes me sleepy. I have tried to talk to him
about it but he becomes incredibly angry and defensive, and
tells me I’m being insensitive. “I don’t think you’re insensitive
for wanting me to suck your dick,” I tell him. “But you like
to suck my dick,” he says. I have just about had it. Any advice?

—Sensitive
Boobs Need Lovin’

Yes:
DTMFA. And if you’re just joining us, SBNL, DTMFA stands for
“dump the motherfucker already,” which is what you need to
do. Your boyfriend is a rude, insensitive asshole, and doesn’t
deserve to have a girlfriend who likes to suck dick. DTMFA.